Zhong Weihui
2013
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Journal
Chinese Journal of Pharmaceuticals
Abstract
2-Oxo-5,6,7,7a-tetrahydrothieno[3,2-c]pyridine,the key intermediate of prasugrel,was synthesized from ethyl 4-oxopiperidine-1-carboxylate by Vilsmerier reaction and cyclization with ethyl mercaptoacetate in the presence of K 2 CO 3 to give diethyl 6,7-dihydro-4H-thieno[3,2-c]pyridine-2,5-dicarboxylate(4),which was subjected to hydrazinolysis,azidation,rearrangement and deprotection to afford ethyl 2-amino-6,7-dihydro-4H-thieno[3,2-c]pyridine5-carboxylate hydrochloride(8),followed by diazotization,hydrolysis,alkaline hydrolysis and salt formation with an overall yield of about 25%.